HipHopWired Featured Video

Ditching the Diddy moniker for his original alias, Puff Daddy, says a lot about where Sean Combs is trying to take things in 2014. He’s returned to the booth to create his upcoming Money Making Mitch LP, and in anticipation of the fur laden visual for “Big Homie,” we’ve celebrated some of the moguls greatest fashion successes and slandered a few of his missteps.

Representing New York to the core, Puff has always made it a point to preserve his fresh. Where artists like Jay Z look best when garbed in a simple outfits and fashion-forward stars like Pharrell can take calculated risks with their looks, the Bad Boy founder’s looks are often as audacious as his character.

Of course, this changed over time (or when his bank account got heftier). Get a sense of Puff Daddy’s style progression — for better or for worse — in the gallery after the jump.

Photo: Instagram

1 2 3 4 5 6 7 8 9 10 11 12 13 14Next page »